EP0777714B1 - Hair shampoos - Google Patents

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Publication number
EP0777714B1
EP0777714B1 EP95929886A EP95929886A EP0777714B1 EP 0777714 B1 EP0777714 B1 EP 0777714B1 EP 95929886 A EP95929886 A EP 95929886A EP 95929886 A EP95929886 A EP 95929886A EP 0777714 B1 EP0777714 B1 EP 0777714B1
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EP
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Prior art keywords
alkyl
fatty acid
ether
hair shampoos
acid
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EP95929886A
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German (de)
French (fr)
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EP0777714A1 (en
Inventor
Bernd Fabry
Jörg KAHRE
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/65—Mixtures of anionic with cationic compounds
    • C11D1/652—Mixtures of anionic compounds with carboxylic amides or alkylol amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/34—Derivatives of acids of phosphorus
    • C11D1/345—Phosphates or phosphites
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group

Definitions

  • the invention relates to hair shampoos with synergistic enhancement of cleansing and foaming power, containing fatty acid N-alkyl polyhydroxyalkylamides and alkyl and / or alkenyl (ether) phosphates.
  • Fatty acid N-alkylpolyhydroxyalkylamides and in particular fatty acid N-methylglucamides are nonionic surfactants which are used, for example, for the production of hand dishwashing detergents because of their good application profile.
  • the use of these substances has been the subject of a large number of publications. Their use as a thickener is known, for example, from European patent application EP-A1 0285768 (Hüls).
  • French published patent application FR-A 1580491 (Henkel) describes aqueous detergent mixtures based on sulfates and / or sulfonates, nonionic surfactants and, if appropriate, soaps, which contain fatty acid N-alkylglucamides as foam regulators.
  • the object of the invention was therefore based on fatty acid N-alkylpolyhydroxyalkylamides to provide, which have an improved cleaning, foam and avivage assets without this benefit due to performance losses in other application technically relevant properties must be paid for.
  • the fatty acid N-alkyl polyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • a reducing sugar with an alkylamine or an alkanolamine
  • acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • US Pat. Nos. 1,985,424, 2,016,962 and 2,703,798 and international patent application WO 92/06984 An overview of this topic by H. Kelkenberg can be found in Tens. Surf.Det. 25 , 8 (1988) .
  • the fatty acid N-alkylpolyhydroxyalkylamides are preferably derived from reducing sugars having 5 or 6 carbon atoms, in particular from glucose.
  • the preferred fatty acid N-alkylpolyhydroxyalkylamides are therefore fatty acid N-alkylglucamides as represented by the formula (II) :
  • the preferred fatty acid N-alkylpolyhydroxyalkylamides used are glucamides of the formula (II) in which R 2 represents hydrogen or an amine group and R 1 CO represents the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, Isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures.
  • R 2 represents hydrogen or an amine group
  • R 1 CO represents the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, Isostearic acid, oleic acid, elaidic acid, petroselini
  • Fatty acid N-alkylglucamides of the formula (II) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C 12/14 coconut fatty acid or a corresponding derivative are particularly preferred.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • Alkyl and / or alkenyl phosphates or ether phosphates are known anionic surfactants which are usually prepared by reacting optionally ethoxylated saturated and / or unsaturated fatty alcohols with phosphorus pentoxide. Depending on the use ratio of the components, technical mixtures are obtained which predominantly contain mono- and dialkyl esters, in addition to triesters, phosphoric acid and unreacted alcohol components. Overviews on this topic are available from RSCooper and G.lmokawa in J.Am.Oil.Chem.Soc.
  • Alkyl and / or alkenyl (ether) phosphates which are suitable for the purposes of the invention follow the formula (III) , in which R 3 represents a linear or branched alkyl radical having 6 to 22 carbon atoms, R 4 represents a group R 1 (OCH 2 CH 2 ) n or X, n represents 0 or numbers 1 to 10 and X represents an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium.
  • R 3 represents a linear or branched alkyl radical having 6 to 22 carbon atoms
  • R 4 represents a group R 1 (OCH 2 CH 2 ) n or X
  • n represents 0 or numbers 1 to 10
  • X represents an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium.
  • Typical examples are oleyl phosphate and mono- and / or dialkyl esters based on adducts of 1 to 10, preferably 2 to 8, moles of ethylene oxide with capron alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol , Oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol and erucyl alcohol and their technical mixtures, which are used, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's monomer synthesis as well as the Roelene monomer synthesis Dimerization of unsaturated fatty alcohols occur.
  • alkyl (ether) phosphates with a degree of esterification in the range from 1 to 2.5 and preferably 1.3 to 2.1 based on addition products of 1 to 5 mol of ethylene oxide in 2-ethylhexanol, and also C 12 / 14 or C 12/18 coconut fatty alcohol and in particular technical oleyl alcohols in the iodine number range 45 to 115, preferably 55 to 95.
  • the hair shampoos are usually produced by stirring aqueous solutions, pastes or concentrates of the input materials, if necessary at a slightly elevated temperature. However, it is also possible to mix spray-dried powder of the two components and then paste or solutions of both ingredients together spray drying and / or granulation to subjugate. All of these cases are purely mechanical processes, chemical ones There is no reaction.
  • the detergent mixtures according to the invention have a synergistic reinforcement of the cleaning and foaming power.
  • the hair shampoos can primarily contain other anionic, nonionic, cationic, amphoteric and / or zwitterionic surfactants as auxiliaries and additives.
  • anionic surfactants are alkylbenzenesulfonates, alkanesulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether, ⁇ -methyl ester sulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, Glycerol ether, Hydroxymischethersulfate, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps , Ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarco
  • anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polygylcol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, alk (en) yloligoglycosides, fatty acid-N-alkylglucamides, protein hydrolysate, sorbate ester products, in particular vegetable ester ester-based sorbate products, especially vegetable-based ester esters, sorbate-based ester products (especially vegetable-based ester esters).
  • nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts.
  • Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are exclusively known compounds.
  • the hair shampoos can contain emulsifiers such as alkoxylated fatty alcohols or sorbitan esters as auxiliaries and additives.
  • emulsifiers such as alkoxylated fatty alcohols or sorbitan esters as auxiliaries and additives.
  • Superfatting agents may be used such as polyethoxylated lanolin derivatives, lecithin derivatives and fatty acid alkanolamides, the latter also serving as foam stabilizers.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone, and electrolytes such as sodium chloride and ammonium chloride.
  • Biogenic active substances are understood to mean, for example, plant extracts, protein hydrolyzates and vitamin complexes.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives and similar compounds.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentadiol or sorbic acid.
  • Suitable pearlizing agents are, for example, glycol distearic esters, such as ethylene, but also fatty acid monoglycol esters.
  • dyes suitable and approved substances can be used for cosmetic purposes, as compiled for example in the publication " Cosmetic Dyes” of the Dye Commission of the German Research Foundation, published by Verlag Chemie, Weinheim, 1984, pp . 81-106 . These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40% by weight on the middle - amount.

Description

Gebiet der ErfindungField of the Invention

Die Erfindung betrifft Haarshampoos mit synergistischer Verstärkung des Reinigungs- und Schaumvermögens, enthaltend Fettsäure-N-alkylpolyhydroxyalkylamide und Alkyl- und/oder Alkenyl(ether)phosphate.The invention relates to hair shampoos with synergistic enhancement of cleansing and foaming power, containing fatty acid N-alkyl polyhydroxyalkylamides and alkyl and / or alkenyl (ether) phosphates.

Stand der TechnikState of the art

Fettsäure-N-alkylpolyhydroxyalkylamide und insbesondere Fettsäure-N-methylglucamide stellen nichtionische Tenside dar, die wegen ihres guten anwendungstechnischen Profils beispielsweise zur Herstellung von Handgeschirrspülmitteln eingesetzt werden. Die Verwendung dieser Stoffe ist Gegenstand einer Vielzahl von Veröffentlichungen. Aus der Europäischen Patentanmeldung EP-A1 0285768 (Hüls) ist beispielsweise ihr Einsatz als Verdickungsmittel bekannt. In der Französischen Offenlegungsschrift FR-A 1580491 (Henkel) werden wäßrige Detergensgemische auf Basis von Sulfaten und/oder Sulfonaten, Niotensiden und gegebenenfalls Seifen beschrieben, die Fettsäure-N-alkylglucamide als Schaumregulatoren enthalten. Gegenstand der Internationalen Patentanmeldungen WO 92/06153; WO 92/06156; WO 92/06157; WO 92/06158; WO 92/06159 und WO 92/06160 (Procter & Gamble) sind Mischungen von Fettsäure-N-alkylglucamiden mit anionischen Tensiden, Tensiden mit Sulfat- und/oder Sulfonatstruktur, Ethercarbonsäuren, Ethersulfaten, Methylestersulfonaten und nichtionischen Tensiden. Die Verwendung dieser Stoffe in den unterschiedlichsten Wasch-, Spül- und Reinigungsmitteln wird in den Internationalen Patentanmeldungen WO 92/06152; WO 92/06154; WO 92/06155; WO 92/06161; WO 92/06162; WO 92/06164; WO 92/06170; WO 92/06171 und WO 92/06172 (Procter & Gamble) beschrieben. In der Praxis hat sich jedoch gezeigt, daß die Fettsäure-N-alkylpolyhydroxyalkylamide auch in Kombination mit anderen vorzugsweise anionischen Tensiden ein Reinigungs- und Schaumvermögen aufweisen, das nicht immer zufriedenstellend sind. Mischungen von Fettsäureglucamiden mit stickstofffreien Tensiden, die dennoch über gute avivierende Eigenschaften verfügen, sind ebenfalls nicht bekannt. Fatty acid N-alkylpolyhydroxyalkylamides and in particular fatty acid N-methylglucamides are nonionic surfactants which are used, for example, for the production of hand dishwashing detergents because of their good application profile. The use of these substances has been the subject of a large number of publications. Their use as a thickener is known, for example, from European patent application EP-A1 0285768 (Hüls). French published patent application FR-A 1580491 (Henkel) describes aqueous detergent mixtures based on sulfates and / or sulfonates, nonionic surfactants and, if appropriate, soaps, which contain fatty acid N-alkylglucamides as foam regulators. Subject of the international patent applications WO 92/06153 ; WO 92/06156; WO 92/06157; WO 92/06158; WO 92/06159 and WO 92/06160 (Procter & Gamble) are mixtures of fatty acid N-alkylglucamides with anionic surfactants, surfactants with a sulfate and / or sulfonate structure, ether carboxylic acids, ether sulfates, methyl ester sulfonates and nonionic surfactants. The use of these substances in a wide variety of detergents, dishwashing detergents and cleaning agents is described in international patent applications WO 92/06152 ; WO 92/06154 ; WO 92/06155; WO 92/06161; WO 92/06162; WO 92/06164; WO 92/06170; WO 92/06171 and WO 92/06172 (Procter & Gamble). In practice, however, it has been found that the fatty acid N-alkylpolyhydroxyalkylamides, in combination with other preferably anionic surfactants, have a cleaning and foaming power which are not always satisfactory. Mixtures of fatty acid glucamides with nitrogen-free surfactants, which nevertheless have good conditioning properties, are also not known.

Die Aufgabe der Erfindung hat somit darin bestanden, auf Basis von Fettsäure-N-alkylpolyhydroxyalkylamiden zur Verfügung zu stellen, die über ein verbessertes Reinigungs-, Schaum- und Avivagevermögen verfügen, ohne daß dieser Vorteil durch Leistungseinbußen in anderen anwendungs technisch relevanten Eigenschaften bezahlt werden muß.The object of the invention was therefore based on fatty acid N-alkylpolyhydroxyalkylamides to provide, which have an improved cleaning, foam and avivage assets without this benefit due to performance losses in other application technically relevant properties must be paid for.

Beschreibung der ErfindungDescription of the invention

Gegenstand der Erfindung sind Haarshampoos mit verbesserter Reinigungsleistung, enthaltend 10 bis 30 Gew.-% - bezogen auf die Mittel -

  • (a) Fettsäure-N-alkylpolyhydroxyalkylamide und
  • (b) Alkyl- und/oder Alkenyl(ether)phosphate
    • im Gewichtsverhältnis 80 : 20 bis 20 : 80 und vorzugsweise 50 : 50 bis 25 : 75.The invention relates to hair shampoos with improved cleaning performance, containing 10 to 30% by weight, based on the composition.
  • (a) Fatty acid N-alkyl polyhydroxyalkylamides and
  • (b) alkyl and / or alkenyl (ether) phosphates
    • in a weight ratio of 80:20 to 20:80 and preferably 50:50 to 25:75.

    Obschon Mischungen auf Basis von Fettsäure-N-alkylpolyhydroxyalkylamiden, insbesondere Fettsäure-N-methylglucamiden und anionischen Tensiden bereits bekannt gewesen sind, wurde überraschenderweise hinsichtlich des Reinigungs- und Schaumvermögens innerhalb bestimmter Mischungsverhältnisse eine starke synergistische Wechselwirkung mit Alkyl- und/oder Alkenyl(ether)phosphaten festgestellt. Die Erfindung schließt die Erkenntnis ein, daß auch hinsichtlich Netzvermögen und Waschleistung eine Verbesserung erzielt wird und die ökotoxikologischen Eigenschaften wenigstens auf dem Niveau der Einzelstoffe erhalten bleiben. Als besonders überraschend hat sich erwiesen, daß der Einsatz insbesondere von ungesättigten Etherphosphaten in Haarreinigungs- und -pflegemitteln im Vergleich zu Produkten, die typische kationische Tenside als Avivagekomponenten enthalten, zu einer Verbesserung der Naß- und Trockenkämmbarkeit führt.Although mixtures based on fatty acid-N-alkylpolyhydroxyalkylamides, especially fatty acid-N-methylglucamides and anionic surfactants have been surprisingly discovered with regard to the cleaning and foaming power within certain mixing ratios a strong synergistic interaction with alkyl and / or alkenyl (ether) phosphates was found. The invention includes the knowledge that also with regard to wetting and washing performance an improvement is achieved and the ecotoxicological properties at least on the The level of the individual substances is retained. It has proven to be particularly surprising that the use in particular of unsaturated ether phosphates in hair cleaning and care products in comparison to products that contain typical cationic surfactants as finishing components, to one Improves wet and dry combability.

    Fettsäure-N-alkylpolyhydroxyalkylamideFatty acid N-alkyl polyhydroxyalkylamides

    Bei den Fettsäure-N-alkylpolyhydroxyalkylamiden handelt es sich um bekannte Stoffe, die üblicherweise durch reduktive Aminierung eines reduzierenden Zuckers mit einem Alkylamin oder einem Alkanolamin und nachfolgende Acylierung mit einer Fettsäure, einem Fettsäurealkylester oder einem Fettsäurechlorid erhalten werden können. Hinsichtlich der Verfahren zu ihrer Herstellung sei auf die US-Patentschriften US 1,985,424, US 2,016,962 und US 2,703,798 sowie die Internationale Patentanmeldung WO 92/06984 verwiesen. Eine Übersicht zu diesem Thema von H.Kelkenberg findet sich in Tens. Surf.Det. 25, 8 (1988). Vorzugsweise leiten sich die Fettsäure-N-alkylpolyhydroxyalkylamide von reduzierenden Zuckern mit 5 oder 6 Kohlenstoffatomen, insbesondere von der Glucose ab. Die bevorzugten Fettsäure-N-alkylpolyhydroxyalkylamide steilen daher Fettsäure-N-alkylglucamide dar, wie sie durch die Formel (II) wiedergegeben werden:

    Figure 00030001
    The fatty acid N-alkyl polyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride. With regard to the processes for their production, reference is made to US Pat. Nos. 1,985,424, 2,016,962 and 2,703,798 and international patent application WO 92/06984 . An overview of this topic by H. Kelkenberg can be found in Tens. Surf.Det. 25 , 8 (1988) . The fatty acid N-alkylpolyhydroxyalkylamides are preferably derived from reducing sugars having 5 or 6 carbon atoms, in particular from glucose. The preferred fatty acid N-alkylpolyhydroxyalkylamides are therefore fatty acid N-alkylglucamides as represented by the formula (II) :
    Figure 00030001

    Vorzugsweise werden als Fettsäure-N-alkylpolyhydroxyalkylamide Glucamide der Formel (II) eingesetzt, in der R2 für Wasserstoff oder eine Amingruppe steht und R1CO für den Acylrest der Capronsäure, Caprylsäure, Caprinsäure, Laurinsäure, Myristinsäure, Palmitinsäure, Palmoleinsäure, Stearinsäure, Isostearinsäure, Ölsäure, Elaidinsäure, Petroselinsäure, Linolsäure, Linolensäure, Arachinsäure, Gadoleinsäure, Behensäure oder Erucasäure bzw. derer technischer Mischungen steht. Besonders bevorzugt sind Fettsäure-N-alkylglucamide der Formel (II), die durch reduktive Aminierung von Glucose mit Methylamin und anschließende Acylierung mit Laurinsäure oder C12/14-Kokosfettsäure bzw. einem entsprechenden Derivat erhalten werden. Weiterhin können sich die Polyhydroxyalkylamide auch von Maltose und Palatinose ableiten.The preferred fatty acid N-alkylpolyhydroxyalkylamides used are glucamides of the formula (II) in which R 2 represents hydrogen or an amine group and R 1 CO represents the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, Isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures. Fatty acid N-alkylglucamides of the formula (II) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C 12/14 coconut fatty acid or a corresponding derivative are particularly preferred. Furthermore, the polyhydroxyalkylamides can also be derived from maltose and palatinose.

    Alkyl- und(oder) Alkenyl(ether)phosphateAlkyl and (or) alkenyl (ether) phosphates

    Alkyl- und/oder Alkenylphosphate bzw. -etherphosphate stellen bekannte anionische Tenside dar, die üblicherweise durch Umsetzung von gegebenenfalls ethoxylierten gesättigten und/oder ungesättigten Fettalkoholen mit Phosphorpentoxid hergestellt werden. In Abhängigkeit des Einsatzverhältnisses der Komponenten werden dabei technische Gemische erhalten, die überwiegend Mono- und Dialkylester, neben Triestern, Phosphorsäure und nicht umgesetzter Alkoholkomponente enthalten. Übersichten zu diesem Thema sind beispielsweise von R.S.Cooper sowie G.lmokawa in J.Am.Oil.Chem.Soc. 41, 337 (1964) bzw. 55, 839 (1978), H.Distler in Tens.Detergents 12, 263 (1975) und O'Lennick in Soap, Cosm.,Chem.Spec. 7, 26 (1986) erschienen. Alkyl- und/oder Alkenyl(ether)phosphate, die im Sinne der Erfindung in Betracht kommen, folgen der Formel (III),

    Figure 00030002
    in der R3 für einen linearen oder verzweigten Alkylrest mit 6 bis 22 Kohlenstoffatomen, R4 für eine Gruppe R1(OCH2CH2)n oder X, n für 0 oder Zahlen von 1 bis 10 und X für ein Alkali- und/oder Erdalkalimetall, Ammonium, Alkylammonium, Alkanolammonium oder Glucammonium steht. Typische Beispiele sind Oleylphosphat sowie Mono- und/oder Dialkylester auf Basis von Addukten von 1 bis 10, vorzugsweise 2 bis 8 Mol Ethylenoxid an Capronalkohol, Caprylalkohol, 2-Ethylhexylalkohol, Caprinalkohol, Laurylalkohol, lsotridecylalkohol, Myristylalkohol, Cetylalkohol, Palmoleylalkohol, Stearylalkohol, Isostearylalkohol, Oleylalkohol, Elaidylalkohol, Petroselinylalkohol, Linolylalkohol, Elaeostearylalkohol, Arachylalkohol, Gadoleylalkohol, Behenylalkohol und Erucylalkohol sowie deren technische Mischungen, die z.B. bei der Hochdruckhydrierung von technischen Methylestem auf Basis von Fetten und Ölen oder Aldehyden aus der Roelen'schen Oxosynthese sowie als Monomerfraktion bei der Dimerisierung von ungesättigten Fettalkoholen anfallen. Besonders bevorzugt ist der Einsatz von Alkyl(ether)phosphaten mit einem Veresterungsgrad im Bereich von 1 bis 2,5 und vorzugsweise 1,3 bis 2,1 auf Basis von Anlagerungsprodukten von 1 bis 5 Mol Ethylenoxid an 2-Ethylhexanol, sowie C12/14-bzw. C12/18-Kokosfettalkohol und insbesondere technische Oleylalkohole im lodzahlbereich 45 bis 115, vorzugsweise 55 bis 95.Alkyl and / or alkenyl phosphates or ether phosphates are known anionic surfactants which are usually prepared by reacting optionally ethoxylated saturated and / or unsaturated fatty alcohols with phosphorus pentoxide. Depending on the use ratio of the components, technical mixtures are obtained which predominantly contain mono- and dialkyl esters, in addition to triesters, phosphoric acid and unreacted alcohol components. Overviews on this topic are available from RSCooper and G.lmokawa in J.Am.Oil.Chem.Soc. 41 , 337 (1964) and 55, 839 (1978) , H.Distler in Tens.Detergents 12 , 263 (1975) and O'Lennick in Soap, Cosm., Chem.Spec. 7 , 26 (1986) . Alkyl and / or alkenyl (ether) phosphates which are suitable for the purposes of the invention follow the formula (III) ,
    Figure 00030002
    in which R 3 represents a linear or branched alkyl radical having 6 to 22 carbon atoms, R 4 represents a group R 1 (OCH 2 CH 2 ) n or X, n represents 0 or numbers 1 to 10 and X represents an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium. Typical examples are oleyl phosphate and mono- and / or dialkyl esters based on adducts of 1 to 10, preferably 2 to 8, moles of ethylene oxide with capron alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol , Oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol and erucyl alcohol and their technical mixtures, which are used, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's monomer synthesis as well as the Roelene monomer synthesis Dimerization of unsaturated fatty alcohols occur. It is particularly preferred to use alkyl (ether) phosphates with a degree of esterification in the range from 1 to 2.5 and preferably 1.3 to 2.1 based on addition products of 1 to 5 mol of ethylene oxide in 2-ethylhexanol, and also C 12 / 14 or C 12/18 coconut fatty alcohol and in particular technical oleyl alcohols in the iodine number range 45 to 115, preferably 55 to 95.

    HaarshampoosHair shampoos

    Die Herstellung der Haarshampoos erfolgt in der Regel durch Verrühren wäßriger Lösungen, Pasten oder Konzentrate der Einsatzstoffe, falls erforderlich bei leicht erhöhter Temperatur. Es ist jedoch ebenfalls möglich, sprühgetrocknete Pulver der beiden Komponenten zu vermischen und anschließend anzupasten oder Lösungen beider Inhaltsstoffe gemeinsam einer Sprühtrocknung und/oder Granulation zu unterwerfen. In allen diesen Fällen handelt es sich um rein mechanische Verfahren, eine chemische Reaktion findet nicht statt.The hair shampoos are usually produced by stirring aqueous solutions, pastes or concentrates of the input materials, if necessary at a slightly elevated temperature. However, it is also possible to mix spray-dried powder of the two components and then paste or solutions of both ingredients together spray drying and / or granulation to subjugate. All of these cases are purely mechanical processes, chemical ones There is no reaction.

    Gewerbliche AnwendbarkeitIndustrial applicability

    Die erfindungsgemäßen Detergensgemische weisen eine synergistische Verstärkung des Reinigungs- und Schaumvermögens auf.The detergent mixtures according to the invention have a synergistic reinforcement of the cleaning and foaming power.

    TensideSurfactants

    Die Haarshampoos können als Hilfs- und Zusatzstoffe in erster Linie weitere anionische, nichtionische, kationische, amphotere und/oder zwitterionische Tenside enthalten. Typische Beispiele für anionische Tenside sind Alkylbenzolsulfonate, Alkansulfonate, Olefinsulfonate, Alkylethersulfonate, Glycerinethersulfonate, α-Methylestersulfonate, Sulfofettsäuren, Alkylsulfate, Fettalkoholethersulfate, Glycerinethersulfate, Hydroxymischethersulfate, Monoglycerid(ether)sulfate, Fettsäureamid(ether)sulfate, Mono- und Dialkylsulfosuccinamate, Sulfotriglyceride, Amidseifen, Ethercarbonsäuren und deren Salze, Fettsäureisethionate, Fettsäuresarcosinate, Fettsäuretauride, Acyllactylate, Alkyloligoglucosidsulfate, Proteinfettsäurekondensate (insbesondere pflanzliche Produkte auf Sojabasis), Sulfosuccinate und Sulfosuccinamate. Sofern die anionischen Tenside Polyglycoletherketten enthalten, können sie eine konventionelle, vorzugsweise jedoch eine eingeengte Homologenverteilung aufweisen. Typische Beispiele für nichtionische Tenside sind Fettalkoholpolyglycolether, Alkylphenolpolyglycolether, Fettsäurepolyglycolester, Fettsäureamidpolygylcolether, Fettaminpolyglycolether, alkoxylierte Triglyceride, Alk(en)yloligoglykoside, Fettsäure-N-alkylglucamide, Proteinhydrolysate (insbesondere pflanzliche Produkte auf Sojabasis) Polyolfettsäureester, Zuckerester, Sorbitanester und Polysorbate. Sofern die nichtionischen Tenside Polyglycoletherketten enthalten, können sie eine konventionelle, vorzugsweise jedoch eine eingeengte Homologenverteilung aufweisen. Typische Beispiele für kationische Tenside sind quartäre Ammoniumverbindungen und Esterquats, insbesondere quaternierte Fettsäuretrialkanolaminester-Salze. Typische Beispiele für amphotere bzw. zwitterionische Tenside sind Alkylbetaine, Alkylamidobetaine, Aminopropionate, Aminoglycinate, lmidazoliniumbetaine und Sulfobetaine. Bei den genannten Tensiden handelt es sich ausschließlich um bekannte Verbindungen. Hinsichtlich Struktur und Herstellung dieser Stoffe sei auf einschlägige Übersichtsarbeiten beispielsweise J.Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, S.54-124 oder J.Falbe (ed.), "Katalysatoren, Tenside und Mineralöladditive", Thieme Verlag, Stuttgart, 1978, S.123-217 verwiesen.The hair shampoos can primarily contain other anionic, nonionic, cationic, amphoteric and / or zwitterionic surfactants as auxiliaries and additives. Typical examples of anionic surfactants are alkylbenzenesulfonates, alkanesulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether, α-methyl ester sulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, Glycerol ether, Hydroxymischethersulfate, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps , Ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, acyl lactylates, alkyl oligoglucoside sulfates, protein fatty acid condensates (especially vegetable products based on soy), sulfosuccinates and sulfosuccinamates. If the anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution. Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polygylcol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, alk (en) yloligoglycosides, fatty acid-N-alkylglucamides, protein hydrolysate, sorbate ester products, in particular vegetable ester ester-based sorbate products, especially vegetable-based ester esters, sorbate-based ester products (especially vegetable-based ester esters). If the nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution. Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts. Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are exclusively known compounds. With regard to the structure and manufacture of these substances, reference is made to relevant reviews, for example J.Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp. 54-124 or J.Falbe (ed.), "Catalysts, Tenside und Mineralöladditive ", Thieme Verlag, Stuttgart, 1978, pp . 123-217 .

    Weitere Hilfs- und ZusatzstoffeOther auxiliaries and additives

    Die Haarshampoos können als Hilfs- und Zusatzstoffe Emulgatoren wie etwa alkoxylierte Fettalkohole oder Sorbitanester enthalten. Als Überfettungsmittel können Substanzen wie beispielsweise polyethoxylierte Lanolinderivate, Lecithinderivate und Fettsäurealkanolamide verwendet werden, wobei die letzteren gleichzeitig als Schaumstabilisatoren dienen. Geeignete Verdickungsmittel sind beispielsweise Polysaccharide, insbesondere Xanthan-Gum, Guar-Guar, Agar-Agar, Alginate und Tylosen, Carboxymethylcellulose und Hydroxyethylcellulose, ferner höhermolekulare Polyethylenglycolmonound -diester von Fettsäuren, Polyacrylate, Polyvinylalkohol und Polyvinylpyrrolidon sowie Elektrolyte wie Kochsalz und Ammoniumchlorid. Unter biogenen Wirkstoffen sind beispielsweise Pflanzenextrakte, Eiweißhydrolysate und Vitaminkomplexe zu verstehen. Gebräuchliche Filmbildner sind beispielsweise Chitosan, mikrokristallines Chitosan, quatemiertes Chitosan, Polyvinylpyrrolidon, Vinylpyrrolidon-Vinylacetat-Copolymerisate, Polymere der Acrylsäurereihe, quatemäre Cellulose-Derivate und ähnliche Verbindungen. Als Konservierungsmittel eignen sich beispielsweise Phenoxyethanol, Formaldehydlösung, Parabene, Pentadiol oder Sorbinsäure. Als Perlglanzmittel kommen beispielsweise Glycoldistearinsäureester wie Ethylenglycoldistearat, aber auch Fettsäuremonoglycolester in Betracht. Als Farbstoffe können die für kosmetische Zwecke geeigneten und zugelassenen Substanzen verwendet werden, wie sie beispielsweise in der Publikation "Kosmetische Färbemittel" der Farb stoffkommission der Deutschen Forschungsgemeinschaft, veröffentlicht im Verlag Chemie, Weinheim, 1984, S.81-106 zusammengestellt sind. Diese Farbstoffe werden üblicherweise in Konzentrationen von 0,001 bis 0,1 Gew.-%, bezogen auf die gesamte Mischung, eingesetzt.The hair shampoos can contain emulsifiers such as alkoxylated fatty alcohols or sorbitan esters as auxiliaries and additives. Superfatting agents may be used such as polyethoxylated lanolin derivatives, lecithin derivatives and fatty acid alkanolamides, the latter also serving as foam stabilizers. Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone, and electrolytes such as sodium chloride and ammonium chloride. Biogenic active substances are understood to mean, for example, plant extracts, protein hydrolyzates and vitamin complexes. Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives and similar compounds. Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentadiol or sorbic acid. Suitable pearlizing agents are, for example, glycol distearic esters, such as ethylene, but also fatty acid monoglycol esters. As dyes suitable and approved substances can be used for cosmetic purposes, as compiled for example in the publication " Cosmetic Dyes " of the Dye Commission of the German Research Foundation, published by Verlag Chemie, Weinheim, 1984, pp . 81-106 . These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.

    Der Gesamtanteil der Hilfs- und Zusatzstoffe kann 1 bis 50, vorzugsweise 5 bis 40 Gew.-% - bezogen auf die Mittel - betragen. The total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40% by weight on the middle - amount.

    BeispieleExamples

    Die Untersuchung des Schaumvermögens erfolgte gemäß Ross-Miles-Test DIN 53901, Teil 2) in einer 1 Gew.-%igen wäßrigen Lösung (Wasserhärte 16°d, Temperatur 20°C). Die Ergebnisse zu Basisschaum und Schaumzerfall sind in Tabelle 1 zusammengefaßt (Prozentangaben als Gew.-%). Die Beispiele 1 bis 9 sind erfindungsgemäß, die Beispiele V1 bis V8 dienen zum Vergleich. Basisschaum und Schaumzerfall Bsp. A B1 B2 C D Schaumhöhe [ml] Basis nach 5 min 1 80 20 - - - 510 420 2 70 30 - - - 520 410 3 60 40 - - - 530 420 4 50 50 - - - 540 440 5 40 60 - - - 570 460 6 40 - 60 - - 550 430 7 30 70 - - - 560 460 8 25 75 - - - 560 460 9 20 80 - - - 500 430 V1 100 - - - - 450 325 V2 - 100 - - - 400 325 V3 - - 100 - - 325 300 V4 - - - 100 - 600 280 V5 - - - - 100 550 350 V6 40 - - 60 - 500 300 V7 40 - - - 60 475 300 V8 0 60 - 40 - 500 400 Legende: (A) C12/14-Kokosfettsäure-N-methylglucamid; (B1) C12/14-Kokosalkyl+3EO-phosphat; Verhältnis Mono/diphosphat = 2:1; (B2) Oleyl+3EO-phosphat, Verhältnis Mono/diphosphat 2:1, Reinheit bezogen auf Oleylalkohol ca. 85 Gew.-%; (C) Dodecylbenzolsulfonat-Na-Salz; (D) C12/14-Kokosfettalkohol+7EO-ethercarboxylat-Na-Salz The foaming power was examined in accordance with the Ross Miles Test DIN 53901, Part 2) in a 1% by weight aqueous solution (water hardness 16 ° d, temperature 20 ° C.). The results for base foam and foam disintegration are summarized in Table 1 (percentages as% by weight). Examples 1 to 9 are according to the invention, Examples V1 to V8 are used for comparison. Base foam and foam breakdown E.g. A B1 B2 C. D Foam height [ml] Base after 5 min 1 80 20th - - - 510 420 2nd 70 30th - - - 520 410 3rd 60 40 - - - 530 420 4th 50 50 - - - 540 440 5 40 60 - - - 570 460 6 40 - 60 - - 550 430 7 30th 70 - - - 560 460 8th 25th 75 - - - 560 460 9 20th 80 - - - 500 430 V1 100 - - - - 450 325 V2 - 100 - - - 400 325 V3 - - 100 - - 325 300 V4 - - - 100 - 600 280 V5 - - - - 100 550 350 V6 40 - - 60 - 500 300 V7 40 - - - 60 475 300 V8 0 60 - 40 - 500 400 Legend: (A) C 12/14 coconut fatty acid N-methylglucamide; (B1) C 12/14 cocoalkyl + 3EO phosphate; Ratio mono / diphosphate = 2: 1; (B2) oleyl + 3EO-phosphate, ratio mono / diphosphate 2: 1, purity based on oleyl alcohol approx. 85% by weight; (C) dodecylbenzenesulfonate Na salt; (D) C 12/14 coconut fatty alcohol + 7EO ether carboxylate Na salt

    Claims (5)

    1. Hair shampoos, characterized in that they contain 10 to 30% by weight, based on the shampoo, of
      (a) fatty acid-N-alkyl polyhydroxyalkylamides and
      (b) alkyl and/or alkenyl (ether) phosphates
      in a ratio by weight of 80:20 to 20:80.
    2. Hair shampoos as claimed in claim 1, characterized in that they contain as component (a) fatty acid-N-alkyl polyhydroxyalkylamides corresponding to formula (I):
      Figure 00090001
      in which R1CO is an aliphatic acyl group containing 6 to 22 carbon atoms, R2 is an alkyl or hydroxyalkyl group containing 1 to 4 carbon atoms and [Z] is a linear or branched polyhydroxyalkyl group containing 3 to 12 carbon atoms and 3 to 10 hydroxyl groups.
    3. Hair shampoos as claimed in claim 2, characterized in that they contain fatty acid-N-alkyl glucamides as component (a).
    4. Hair shampoos as claimed in claims 1 to 3, characterized in that they contain as component (b) alkyl and/or alkenyl (ether) phosphates corresponding to formula (III):
      Figure 00090002
      in which R3 is a linear or branched alkyl group containing 6 to 22 carbon atoms, R'is a group R1(OCH2CH2)n or X, n is 0 or a number of 1 to 10 and X is an alkali metal and/or alkaline earth metal, ammonium, alkyl ammonium, alkanolammonium or glucammonium.
    5. Hair shampoos as claimed in claims 1 to 4, characterized in that they contain components (a) and (b) in a ratio by weight of 50:50 to 25:75.
    EP95929886A 1994-08-25 1995-08-16 Hair shampoos Expired - Lifetime EP0777714B1 (en)

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    DE4430085A DE4430085C2 (en) 1994-08-25 1994-08-25 Hair shampoos
    DE4430085 1994-08-25
    PCT/EP1995/003259 WO1996006150A1 (en) 1994-08-25 1995-08-16 Detergent mixtures with improved cleansing power

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    Publication Number Publication Date
    EP0777714A1 EP0777714A1 (en) 1997-06-11
    EP0777714B1 true EP0777714B1 (en) 1999-01-20

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    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    CN110898997A (en) * 2018-09-17 2020-03-24 中蓝连海设计研究院有限公司 Spodumene collecting agent and using method and application thereof

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    * Cited by examiner, † Cited by third party
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    DE19840342A1 (en) * 1998-09-04 2000-03-09 Clariant Gmbh Solid surfactant mixtures containing fatty acid polyhydroxyamides

    Family Cites Families (5)

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    DE69118193T2 (en) * 1990-09-28 1996-11-14 Procter & Gamble DETERGENT CONTAINING ALKYL SULFATE AND POLYHYDROXY FATTY ACID AMIDTENSIDE
    DE69118194T2 (en) * 1990-09-28 1996-11-14 Procter & Gamble DETERGENT COMPOSITIONS CONTAINING POLYHYDROXY FATTY ACID AND ALKOXYLATED ALKYL SULFATE
    EP0522206B1 (en) * 1991-07-08 1995-09-20 The Procter & Gamble Company Detergent compositions containing polyhydroxy fatty acid amide surfactants and a clay softening system
    DE4229442A1 (en) * 1992-09-03 1994-03-10 Henkel Kgaa Dispersant
    EP0592754A1 (en) * 1992-10-13 1994-04-20 The Procter & Gamble Company Fluid compositions containing polyhydroxy fatty acid amides

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    CN110898997A (en) * 2018-09-17 2020-03-24 中蓝连海设计研究院有限公司 Spodumene collecting agent and using method and application thereof
    CN110898997B (en) * 2018-09-17 2022-03-22 中蓝连海设计研究院有限公司 Spodumene collecting agent and using method and application thereof

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